Formaldehyde → HCID 91506916, compound

HRID 459936Notes

Reaction equation

HRID 459936 reaction equation
Cl.[F:2][C:3]([F:35])([F:34])[C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:7][N:8]([CH3:26])[C:9]([N:11]1[C@@H:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[CH3:25])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10].C=O.[C:38](OC(OC(=O)C)(OC(=O)C)C(O[BH3-])=O)(=O)C.[Na+]>ClCCCl>[F:35][C:3]([F:34])([F:2])[C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:29]=1)[CH2:7][N:8]([CH3:26])[C:9]([N:11]1[C@@H:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[CH3:25])[CH2:16][CH2:15][N:14]([CH3:38])[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 131726309HCID 131726309, compoundHCID 131726311HCID 131726311, compound

Product 1

HCID 91506916HCID 91506916, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of example 2 (53 mg), aqueous formaldehyde (33 μL) and sodium triacetoxyacetoxyborohydride (50 mg) in anhydrous 1,2-dichloroethane (2 mL) was stirred at r.t. overnight. The mixture was washed with water (2 mL) and brine (2 mL) and concentrated in vacuo. The residue was purified by flash chromatography (AcOEt 100%) to give 7-(R)-(4-fluoro-2-methyl-phenyl)-4-methyl-[1,4]-diazepane-1-carboxylic acid, (3,5-bis-trifluoromethyl-benzyl)-methylamide (12 mg).

Workup

  1. washThe mixture was washed with water (2 mL) and brine (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (AcOEt 100%)

Sources & evidence

ORD record
ord-5a73216b8f3a4996a9c4c76b480dcb5a
Source dataset
uspto-grants-2007_03
Patent number
US07196077B2

Reaction notes

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